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2D Structure
Also known as: 173553-37-2, 107220-28-0, Cevimeline hydrochloride, 2-methyl-1'-azaspiro[[1,3]oxathiolane-5,3'-bicyclo[2.2.2]octane] (hydrochloride), Cevimeline hcl, 2-methylspiro[1,3-oxathiolane-5,3'-1-azabicyclo[2.2.2]octane];hydrochloride
Molecular Formula
C10H18ClNOS
Molecular Weight
235.77  g/mol
InChI Key
SURWTGAXEIEOGY-UHFFFAOYSA-N

Cevimeline Hydrochloride is a cholinergic analogue with glandular secretion stimulatory activity. Cevimeline binds to and activates muscarinic receptors, thereby increasing the secretions in exocrine salivary and sweat glands. This cholinergic agonist also increases the tone of smooth muscle in the gastrointestinal and urinary tracts. Cevimeline is being studied as a treatment for dry mouth caused by radiation therapy to the head and neck.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-methylspiro[1,3-oxathiolane-5,3'-1-azabicyclo[2.2.2]octane];hydrochloride
2.1.2 InChI
InChI=1S/C10H17NOS.ClH/c1-8-12-10(7-13-8)6-11-4-2-9(10)3-5-11;/h8-9H,2-7H2,1H3;1H
2.1.3 InChI Key
SURWTGAXEIEOGY-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1OC2(CN3CCC2CC3)CS1.Cl
2.2 Synonyms
2.2.1 MeSH Synonyms

1. 2-methyspiro(1,3-oxathiolane-5,3)quinuclidine

2. Af 102b

3. Af 102b, (cis-(+))-isomer

4. Af 102b, (trans)-isomer

5. Af-102b

6. Af102b

7. Cevimeline

8. Cevimeline Hydrochloride

9. Evoxac

10. Fks 508

11. Fks-508

12. Sni 2011

13. Sni-2011

2.2.2 Depositor-Supplied Synonyms

1. 173553-37-2

2. 107220-28-0

3. Cevimeline Hydrochloride

4. 2-methyl-1'-azaspiro[[1,3]oxathiolane-5,3'-bicyclo[2.2.2]octane] (hydrochloride)

5. Cevimeline Hcl

6. 2-methylspiro[1,3-oxathiolane-5,3'-1-azabicyclo[2.2.2]octane];hydrochloride

7. 2-methyl-1'-azaspiro[[1,3]oxathiolane-5,3'-bicyclo[2.2.2]octane] Hydrochloride

8. Spiro[1-azabicyclo[2.2.2]octane-3,5'-[1,3]oxathiolane], 2'-methyl-,hydrochloride

9. Af-102b

10. Schembl861315

11. Dtxsid701338114

12. Bcp12519

13. Cs-b1634

14. Yga55337

15. Akos037650732

16. Cs-15234

17. Ft-0664491

18. A925456

19. J-001739

20. (+/-)-cis-2-methylspiro[1,3-oxathiolane-5,3'-quinuclidine]

21. Cis-2-methylspiro[1,3-oxathiolane-5,3'-quinuclidine]hydrochloride

22. 2-methyl-1'-azaspiro[[1,3]oxathiolane-5,3'-bicyclo[2.2.2]octane] (hcl)

23. 5'-methyl-4-azaspiro[bicyclo[2.2.2]octane-2,2'-[1,4]oxathiolane] Hydrochloride

2.3 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 235.77 g/mol
Molecular Formula C10H18ClNOS
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass235.0797631 g/mol
Monoisotopic Mass235.0797631 g/mol
Topological Polar Surface Area37.8 Ų
Heavy Atom Count14
Formal Charge0
Complexity215
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count2
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Muscarinic Agonists

Drugs that bind to and activate muscarinic cholinergic receptors (RECEPTORS, MUSCARINIC). Muscarinic agonists are most commonly used when it is desirable to increase smooth muscle tone, especially in the GI tract, urinary bladder and the eye. They may also be used to reduce heart rate. (See all compounds classified as Muscarinic Agonists.)


Parasympathomimetics

Drugs that mimic the effects of parasympathetic nervous system activity. Included here are drugs that directly stimulate muscarinic receptors and drugs that potentiate cholinergic activity, usually by slowing the breakdown of acetylcholine (CHOLINESTERASE INHIBITORS). Drugs that stimulate both sympathetic and parasympathetic postganglionic neurons (GANGLIONIC STIMULANTS) are not included here. (See all compounds classified as Parasympathomimetics.)


4.2 FDA Pharmacological Classification
4.2.1 Pharmacological Classes
Cholinergic Receptor Agonist [EPC]; Cholinergic Muscarinic Agonists [MoA]